KR950032068A - Method for preparing substituted benzoyl fatty acid derivatives - Google Patents

Method for preparing substituted benzoyl fatty acid derivatives Download PDF

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KR950032068A
KR950032068A KR1019950006966A KR19950006966A KR950032068A KR 950032068 A KR950032068 A KR 950032068A KR 1019950006966 A KR1019950006966 A KR 1019950006966A KR 19950006966 A KR19950006966 A KR 19950006966A KR 950032068 A KR950032068 A KR 950032068A
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alkyl group
palladium
hydrogen atom
halo
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KR100190473B1 (en
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아키히코 요시우라
노보루 아베
마사아키 구도
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무라타 도시카즈
니혼노야쿠 가부시키가이샤
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
    • C07C255/13—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

본 발명은 다음에 나타낸 반응식에 따라, 일반식(I)의 치환된 벤조일 지방산 유도체를 제조하는 방법에 관한 것이며, 본 발명은 재활용성 촉매의 존재하에 저렴한 재료로부터 고수율로 치환된 벤조일 지방산 유도체를 제조 할 수 있게 한다.The present invention relates to a process for preparing substituted benzoyl fatty acid derivatives of general formula (I) according to the reaction scheme shown below, and the present invention relates to benzoyl fatty acid derivatives substituted in high yield from inexpensive materials in the presence of a recyclable catalyst. To be manufactured.

상기 식에서, R은 H또는 -OC(R3)(R4)-R5〔여기에서, R3및 R4는 각각 H 또는 C1-6알킬 그룹이고ㅡ R5는 시아노 그룹, -CON(R6)R7(여기서, R6및R7는 각각 H 또는 C1-6알킬 그룹이다) 또는 -COAR8(여기서, R8는 H 또는 C1-6알킬그룹이고, A는 산소 또는 S 이다)〕이고, R1및 R2는 각각 H 또는 C1-6알킬그룹이며, 는 각각 할로겐 원자이고, n은 1 내지 3의 정수이며, Hal은 할로겐 원자이고, R9는 C1-6알킬그룹, 비치화된 페닐그룹, 또는 할로겐원자, C1-6알킬그룹, C1-6알콕시그룹, 할로 C1-6알콕시그룹, C1-6알킬티오 그룹 및 할로 - C1-6알킬티오 그룹으로 구성된 그룹으로부터 선택되는 하나 이상의 치환제를 갖는 치환된 페닐 그룹이다.Wherein R is H or -OC (R 3 ) (R 4 ) -R 5 , wherein R 3 and R 4 are each H or a C 1-6 alkyl group and R 5 is a cyano group, -CON (R 6 ) R 7 where R 6 and R 7 are each H or C 1-6 alkyl groups or -COAR 8 where R 8 is H or C 1-6 alkyl groups and A is oxygen or and it S a)], R 1 and R 2 are each H or C 1-6 alkyl group, are each a halogen atom, n is an integer from 1 to 3, and Hal is a halogen atom, R 9 is C 1- 6 alkyl group, unsubstituted phenyl group, or halogen atom, C 1-6 alkyl group, C 1-6 alkoxy group, halo C 1-6 alkoxy group, C 1-6 alkylthio group and halo-C 1-6 Substituted phenyl group having one or more substituents selected from the group consisting of alkylthio groups.

Description

치환된 벤조일 지방산 유도체의 제조 방법.Process for preparing substituted benzoyl fatty acid derivatives.

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (8)

염기, 팔라듐 화합물 및 하나 이상의 인 화합물의 존재하에 일반식(Ⅱ)의 치환된 펜아실 할라이드 유도체를 일반식(Ⅲ)의 화합물 및 일산화탄소와 반응시킴을 포함하여, 일반식(I)의 치환된 벤조일 지방산 유도체를 제조하는 방법.Substituted benzoyl of Formula (I), including reacting a substituted phenacyl halide derivative of Formula (II) with a compound of Formula (III) and carbon monoxide in the presence of a base, a palladium compound and one or more phosphorus compounds Method for preparing fatty acid derivatives. 상기 식에서, R은 수소원자 또는 -O-C(R3)(R4)-R5〔여기에서, R3및 R4는 동일하거나 상이할 수 있으며, 수소원자 또는 C1-6알킬그룹이고 R5는 시아노 그룹, -CON(R6)R7(여기서, R6및R7는 동일하거나 상이할 수 있으며, 수소원자 또는 C1-6알킬그룹이다) 또는 -COAR8(여기서, R8는 수소원자 또는 C1-6알킬 그룹이고 A는 산소원자 또는 황원자이다)이다〕이고 R1및 R2는 각각 수소원자 또는 C1-6알킬 그룹이며, R9는 C1-6알킬그룹, 비치화된 페닐그룹, 또는 할로겐원자, C1-6알킬그룹, 할로 C1-6알킬그룹, C1-6알콕시 그룹 및 할로 - C1-6알콕시 그룹, C|1-6알킬티오 그룹 및 할로C1-6알킬티오 그룹으로 구성된 그룹으로부터 선택되는 하나 이상의 치환체를 갖는 치환된 페닐 그룹이고, X는 동일하거나 상이할 수 있으며 할로겐 원자를 나타내고, n은 1 내지 3의 정수이고 Hal은 할로겐 원자인데, 단 R은 수소원자인 경우 Hal은 브룸원자를 포함하지 않는다.Wherein R is a hydrogen atom or -OC (R 3 ) (R 4 ) -R 5 , wherein R 3 and R 4 may be the same or different and are a hydrogen atom or a C 1-6 alkyl group and R 5 Is a cyano group, -CON (R 6 ) R 7 (wherein R 6 and R 7 may be the same or different and is a hydrogen atom or a C 1-6 alkyl group) or -COAR 8 (where R 8 is Hydrogen atom or C 1-6 alkyl group and A is oxygen atom or sulfur atom), and R 1 and R 2 are each hydrogen atom or C 1-6 alkyl group, and R 9 is C 1-6 alkyl group, Phenyl group, or halogen atom, C 1-6 alkyl group, halo C 1-6 alkyl group, C 1-6 alkoxy group and halo-C 1-6 alkoxy group, C | 1-6 alkylthio group and a halo-C 1-6 substituted phenyl group having one or more substituents selected from the group consisting of an alkyl thio group, X may be the same or different and represents a halogen atom, n is from 1 to 3 Is an integer of and Hal is a halogen atom, provided that R is a hydrogen atom and Hal does not include a broom atom. 제1항에 있어서, 팔라듐 화합물이 금속 팔라듐, 또는 고체상에 지지된 0가 또는 2가 팔라듐 착물인 방법.The method of claim 1 wherein the palladium compound is a metal palladium, or a zero or divalent palladium complex supported on a solid phase. 제2항에 있어서, 팔라듐 화합물이 팔라듐-탄소, 팔라듐 클로라이드, 팔라듐 아세테이트, 테트라키스(트리페닐포스핀)팔라듐, 디클로로비스(벤조니트릴)팔라듐, 디클로로비스(아세토니트릴) 팔라듐 또는 디클로로비스(트리페닐포스핀)팔라듐인 방법.The method of claim 2, wherein the palladium compound is palladium-carbon, palladium chloride, palladium acetate, tetrakis (triphenylphosphine) palladium, dichlorobis (benzonitrile) palladium, dichlorobis (acetonitrile) palladium or dichlorobis (triphenyl Phosphine) palladium. 제1항에 있어서, 인 화합물이 트리알킬포스핀, 트리알킬 포스파이트, 트리아릴 포스파이트 및 다음 일반식(Ⅳ)의 화합물로 구성된 그룹으로부터 선택되는 방법.The process of claim 1 wherein the phosphorus compound is selected from the group consisting of trialkylphosphines, trialkyl phosphites, triaryl phosphites and compounds of the following general formula (IV). (R')2-P-Y-P-(R')2(Ⅳ)(R ') 2 -PYP- (R') 2 (Ⅳ) 상기식에서, R'은 C1-6알킬 그룹,비치환된 페닐 그룹, 또는 할로겐 원자, C1-6알킬그룹, 할로- C1-6알킬그룹, C1-6알콕시 그룹, 할로- C|1-6알콕시 그룹, C1-6알킬티오 및 할로- C1-6알킬티오 그룹으로 구성된 그룹으로부터 선택되는 하나 이상의 치환제를 갖는 치환된 페닐 그룹이고, Y는 C1-6알킬렌 그룹이다.Is a C 1-6 alkyl group, an unsubstituted phenyl group, or a halogen atom, a C 1-6 alkyl group, a halo-C 1-6 alkyl group, a C 1-6 alkoxy group, a halo-C | Is a substituted phenyl group having at least one substituent selected from the group consisting of 1-6 alkoxy groups, C 1-6 alkylthio and halo-C 1-6 alkylthio groups, and Y is a C 1-6 alkylene group . 제1항에 있어서, 염기가 탄산수소나트륨 또는 나트륨 아세테이트인 방법.The method of claim 1 wherein the base is sodium bicarbonate or sodium acetate. 염기 및 옥타카보닐디코발트의 존재하에 일반식(Ⅱ)의 치환된 펜아실 할라이드 유도체를 일반식(Ⅲ)의 화합물 및 일산화탄소와 반응시킴을 포함하여 일반식(I) 의 치환된 벤조일 지방산 유도체를 제조하는 방법.Preparation of Substituted Benzoyl Fatty Acid Derivatives of Formula (I) Including Reaction of Substituted Penacyl Halide Derivatives of Formula (II) with Compounds of Formula (III) and Carbon Monoxide in the Presence of Base and Octacarbonyldicobalt How to. 상기 식에서, R은 수소원자 또는 -O-C(R3)(R4)-R5〔여기에서, R3및 R4는 동일하거나 상이할 수 있으며, 수소원자 또는 C1-6알킬그룹이고 R5는 시아노 그룹, -CON(R6)R7(여기서, R6및R7는 동일하거나 상이할 수 있으며, 수소원자 또는 C1-6알킬그룹이고 R5는 시아노 그룹, -CON(R6)R7(여기서, R6및R7는 동일하거나 상이할수 있으며, 수소원자 또는 C1-6</SB 알킬그룹이다) 또는 -COAR 8(여기서, R8는 수소원자 또는 C1-6알킬그룹이고 A는 산소원자 또는 황원자이다)이다〕이고 R1및 R2는 각각 수소원자 또는 C1-6알킬그룹이고, R9는 C1-6알킬그룹, 비치화된 페닐그룹, 또는 할로겐원자, C1-6알킬그룹, 할로 C1-6알킬그룹, C1-6알콕시 그룹 , 할로 - C1-6알콕시 그룹, C1-6알킬티오 그룹 및 할로C1-6알킬티오 그룹으로 구성된 그룹으로부터 선택되는 동일하거나 상이할 수 있는 하나 이상의 치환체를 갖는 치환된 페닐 그룹이며, X는 동일하거나 상이할 수 있으며 할로겐 원자이고, n은 1 내지 3의 정수이며 Hal은 할로겐 원자이다.Wherein R is a hydrogen atom or -OC (R 3 ) (R 4 ) -R 5 , wherein R 3 and R 4 may be the same or different and are a hydrogen atom or a C 1-6 alkyl group and R 5 Is a cyano group, -CON (R 6 ) R 7 , wherein R 6 and R 7 may be the same or different, a hydrogen atom or a C 1-6 alkyl group and R 5 is a cyano group, -CON (R 6 ) R 7 (wherein R 6 and R 7 may be the same or different and is a hydrogen atom or a C 1-6 </ SB alkyl group) or -COAR 8 (where R 8 is a hydrogen atom or C 1-6 Alkyl group and A is an oxygen atom or a sulfur atom), and R 1 and R 2 are each a hydrogen atom or a C 1-6 alkyl group, and R 9 is a C 1-6 alkyl group, an unsubstituted phenyl group, or a halogen. With atoms, C 1-6 alkyl groups, halo C 1-6 alkyl groups, C 1-6 alkoxy groups, halo-C 1-6 alkoxy groups, C 1-6 alkylthio groups and haloC 1-6 alkylthio groups Same selected from configured groups Or a substituted phenyl group having at least one substituent which may be different, X may be the same or different and is a halogen atom, n is an integer from 1 to 3 and Hal is a halogen atom. 제6항에 있어서, 염기가 유기 염기인 방법.The method of claim 6, wherein the base is an organic base. 제7항에 있어서, 유기 염기가 트리에틸아민 또는 나트륨 아세테이트인 방법.8. The method of claim 7, wherein the organic base is triethylamine or sodium acetate. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019950006966A 1994-03-31 1995-03-30 Process for producing a substituted benzoyl fatty acid KR100190473B1 (en)

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DE10015279A1 (en) 2000-03-28 2001-10-04 Bayer Ag Process for the preparation of N-butyryl-4-amino-3-methyl-benzoic acid methyl ester and the new compound N- (4-bromo-2-methylphenyl) butanamide

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DE69517461D1 (en) 2000-07-20
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CN1115313A (en) 1996-01-24
IL113200A (en) 1999-03-12
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IL113200A0 (en) 1995-06-29
DE69517461T2 (en) 2000-10-26

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